Electron ionization mass spectra of acetals ofβ-D-glycopyranosylnitromethanes

✍ Scribed by Kováčik, Vladimír; Pätoprstý, Vladimír; Lattová, Erika; Petruš, Ladislav; Ovcharenko, Vladimir; Pihlaja, Kalevi

• Publisher: John Wiley and Sons
• Year: 1999
• Tongue: English
• Weight: 87 KB
• Volume: 34
• Category: Article
• ISSN: 1076-5174
• DOI: 10.1002/(sici)1096-9888(199912)34:12<1322::aid-jms888>3.0.co;2-#

✦ Synopsis

O-Isopropylidene and O-benzylidene acetals of common 2,6-anhydro-1-deoxy-1-nitroalditols (b-D-glycopyranosylnitromethanes) derived from D-glucose, D-galactose and D-mannose were studied by electron ionization (EI) mass spectrometry. Fragment pathways of the title compounds were studied using accurate mass measurements, collision-induced dissociation, B/E and B 2 /E measurements of selected ions and mass spectra of O-deuterium-labelled compound. The fragmentation pathways and some differences found among the mass spectra of stereoisomers are discussed. Noteworthy is the splitting off of the ž NO 2 radical and elimination of acetone from the molecular ions of 4,6-O-benzylidene-2,3-O-isopropylidene-b-D-galactopyranosylnitromethane. This fragmentation route of relatively high abundance was not observed in the case of D-gluco and D-manno analogues. The differences in the EI mass spectra of stereoisomers may help to provide some information serving for the estimation of the stereochemical arrangement of compounds of this type.